Details of the Drug

General Information of Drug (ID: DM2EXC5)

Drug Name
BOL-303259-X
Synonyms
Latanoprostene bunod; Latanoprostene bunod); NCX-116; PF-03187207; PF-3187207; BOL-303259-X1; NO donors (glaucoma), NicOx/Pfizer; NO-donating prostaglandin F2-alpha analogs (glaucoma), Pfizer; NO-donating prostaglandin F2-alpha analogs (glaucoma), NicOx/Pfizer; Nitric oxide-donating prostaglandin F2-alpha analogs (eye disease), NicOx/Pfizer; NO-donating prostaglandin F2-alpha analogs (glaucoma), NicOx/ Bausch & Lomb
Indication
Disease Entry ICD 11 Status REF
Open-angle glaucoma 9C61 Approved [1]
Renal cell carcinoma 2C90 Phase 3 [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 2 Molecular Weight (mw) 507.6
Logarithm of the Partition Coefficient (xlogp) 4.4
Rotatable Bond Count (rotbonds) 18
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 8
ADMET Property
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 59.1 ng/L []
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 5 min []
Half-life
The concentration or amount of drug in body reduced by one-half in 1.8 hours (in rabbits cornea), 2.1 hours (in rabbits aqueous humor), and 4.6 hours (in rabbits iris/ciliary body) [3]
Metabolism
The drug is metabolized via the endogenous corneal esterases into latanoprost acid and butanediol mononitrate []
Chemical Identifiers
Formula
C27H41NO8
IUPAC Name
4-nitrooxybutyl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate
Canonical SMILES
C1[C@H]([C@@H]([C@H]([C@H]1O)C/C=C\\CCCC(=O)OCCCCO[N+](=O)[O-])CC[C@H](CCC2=CC=CC=C2)O)O
InChI
InChI=1S/C27H41NO8/c29-22(15-14-21-10-4-3-5-11-21)16-17-24-23(25(30)20-26(24)31)12-6-1-2-7-13-27(32)35-18-8-9-19-36-28(33)34/h1,3-6,10-11,22-26,29-31H,2,7-9,12-20H2/b6-1-/t22-,23+,24+,25-,26+/m0/s1
InChIKey
LOVMMUBRQUFEAH-UIEAZXIASA-N
Cross-matching ID
PubChem CID
11156438
CAS Number
860005-21-6
DrugBank ID
DB11660
TTD ID
D05LQX
VARIDT ID
DR00093
ACDINA ID
D01200
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Prostaglandin F2-alpha receptor (PTGFR) TTT2ZAR PF2R_HUMAN Agonist [4]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Organic anion transporting polypeptide 2B1 (SLCO2B1) DTPFTEQ SO2B1_HUMAN Substrate [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Open-angle glaucoma
ICD Disease Classification 9C61
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Prostaglandin F2-alpha receptor (PTGFR) DTT PTGFR 8.25E-02 -0.05 -0.14
Organic anion transporting polypeptide 2B1 (SLCO2B1) DTP OATP2B1 6.30E-05 2.52E-01 5.88E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Edetic acid E00094 6049 Antimicrobial preservative; Complexing agent
Glycerin E00026 753 Antimicrobial preservative; Emollient; Flavoring agent; Humectant; Lubricant; Plasticizing agent; Solvent; Suppository base; Tonicity agent; Viscosity-controlling agent
Polysorbate 80 E00665 Not Available Dispersing agent; Emollient; Emulsifying agent; Plasticizing agent; Solubilizing agent; Surfactant; Suspending agent
Water E00035 962 Solvent
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Latanoprostene Bunod 0.24 mg/ml solution 0.24 mg/ml Solution Topical
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 Evaluation of the Effect of Latanoprostene Bunod Ophthalmic Solution, 0.024% in Lowering Intraocular Pressure over 24 in Healthy Japanese Subjects.Adv Ther. 2015 Nov;32(11):1128-39.
2 ClinicalTrials.gov (NCT01895972) A Study Evaluating the Long-Term Safety of Latanoprostene Bunod Ophthalmic Solution 0.024%, in Japanese Subjects With Open-Angle Glaucoma or Ocular Hypertension. U.S.National Institutes of Health.
3 Critical evaluation of latanoprostene bunod in the treatment of glaucoma. Clin Ophthalmol. 2016 Oct 18;10:2035-2050. eCollection 2016.
4 Ocular hypotensive activity of BOL-303259-X, a nitric oxide donating prostaglandin F2alpha agonist, in preclinical models. Exp Eye Res. 2011 Sep;93(3):250-5.
5 The prostaglandin transporter OATP2A1 is expressed in human ocular tissues and transports the antiglaucoma prostanoid latanoprost. Invest Ophthalmol Vis Sci. 2010 May;51(5):2504-11.